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acemetacin
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Name

acemetacin

 EINECS 258-403-4
CAS No. 53164-05-9 Density 1.36 g/cm3
PSA 94.83000 LogP 3.47050
Solubility N/A Melting Point 151.5 °C
Formula C21H18ClNO6 Boiling Point 565.5 °C at 760 mmHg
Molecular Weight 415.83 Flash Point 295.8 °C
Transport Information UN 2811 Appearance Light yellow solid
Safety 22-25-36/37/39-45 Risk Codes 26/27/28
Molecular Structure Molecular Structure of 53164-05-9 (Acemetacin) Hazard Symbols VeryT+
Synonyms

1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-aceticacid carboxymethyl ester;1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-aceticacid carboxymethyl ester;2-[2-[1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl]acetyloxy]aceticacid;Acemet;Acemethacin;Acemix;Emflex;K 708;Rantudil;Rheumibis;Rheutrop;Solart;TV 1322;TVX 1322;

Article Data 14

acemetacin Synthetic route

75302-98-6

acemetacin tert-butyl ester

53164-05-9

acemetacin

Conditions
ConditionsYield
With hydrogenchloride; acetic anhydride In acetic acid at 80℃; for 5h; Large scale;99.45%
With trifluoroacetic acid In dichloromethane at 20℃; for 48h;80%
1601-20-3

2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid tert-butyl ester

64-19-7

acetic acid

53164-05-9

acemetacin

Conditions
ConditionsYield
With hydrogenchloride; aluminum (III) chloride at 60℃; for 5h; Reagent/catalyst; Temperature; Large scale;98.8%
53164-04-8

<1-(4-Chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy>essigsaeurebenzylester

53164-05-9

acemetacin

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 80℃; for 24h; Temperature;97.8%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 20h;95%
With hydrogen; palladium on activated charcoal In ethyl acetate at 40℃; for 1h;93%
75302-98-6

acemetacin tert-butyl ester

A

53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

B

53164-05-9

acemetacin

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 20℃; for 6h; chemoselective reaction;A 30%
B 66%
19501-58-7

4-methoxyphenylhydrazine hydrochloride

53164-05-9

acemetacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C
2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C
3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C
View Scheme
53164-08-2

(5-Methoxy-2-methylindol-3-acetoxy)essigsaeurebenzylester

53164-05-9

acemetacin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / various solvent(s) / 3 h / 190 - 195 °C
2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C
View Scheme
53-86-1

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

53164-05-9

acemetacin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) K2CO3 / 1.) DMF, 45 min, 50 deg C, 2.) 3 h, 50 deg C
2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C
View Scheme
123-76-2

levulinic acid

phosphorus pentasulfide

phosphorus pentasulfide

53164-05-9

acemetacin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) K2CO3 / 1.) DMF, 70 min, 40 deg C, 2.) 4 h, 50 deg C
2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C
3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C
4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C
View Scheme
53164-03-7

Laevulinoyloxyessigsaeurebenzylester

53164-05-9

acemetacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C
2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C
3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C
View Scheme

4-Methoxyphenylhydrazin-β-sulfonsaeure Natriumsalz

53164-05-9

acemetacin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 68 percent / conc. HCl / H2O / 2 h / 20 °C
2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C
3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C
4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C
View Scheme

acemetacin Chemical Properties

Systematic (IUPAC) name :2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyacetic acid
Formula: C21H18ClNO6 
Mol. mass :415.82372 g/mol

acemetacin History

Acemetacin  is manufactured by Merck under the tradename Emflex, and is available in the UK as a prescription-only drug.

acemetacin Uses

    Acemetacin is a non-steroidal anti-inflammatory drug, used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain.
    Acemetacin, a glycolic acid ester of indometacin, acts as a prodrug; in the body, it is metabolized to indometacin, which then acts as an inhibitor of cyclooxygenase, producing the anti-inflammatory effects.

acemetacin Consensus Reports

    An advantage of acemetacin is that it reduces gastric damage when compared to indometacin.
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